NP-MRD: Showing NP-Card for (3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate (NP0244099)

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Record Information

Version

1.0

Created at

2022-09-07 04:48:14 UTC

Updated at

2022-09-07 04:48:14 UTC

NP-MRD ID

NP0244099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate

Description

7-Oxo-cytochalasin C belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. (3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate is found in Xylaria longipes. Based on a literature review very few articles have been published on 7-oxo-cytochalasin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206482D          

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M  END

     RDKit          3D

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  Mrv1652309072206482D          

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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 22  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 34  1  1  0  0  0
  5 36  1  0  0  0  0
 17 36  1  0  0  0  0
 24 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244099

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C\[C@H]2C(=O)C(C)=C(C)[C@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]23[C@H](OC(C)=O)\C=C\[C@H](C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H35NO5/c1-17-10-9-13-23-28(34)20(4)19(3)26-24(16-22-11-7-6-8-12-22)31-29(35)30(23,26)25(36-21(5)32)15-14-18(2)27(17)33/h6-9,11-15,17-18,23-26H,10,16H2,1-5H3,(H,31,35)/b13-9+,15-14+/t17-,18-,23-,24-,25+,26-,30+/m0/s1

> <INCHI_KEY>
ZLQPFOHITPCQQO-QCKAJGFESA-N

> <FORMULA>
C30H35NO5

> <MOLECULAR_WEIGHT>
489.612

> <EXACT_MASS>
489.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.03163644103067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

> <JCHEM_LOGP>
4.54122386144815

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.74217204987831

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0606870469910783

> <JCHEM_PKA_STRONGEST_BASIC>
5.4523672191545725

> <JCHEM_POLAR_SURFACE_AREA>
93.03

> <JCHEM_REFRACTIVITY>
140.65400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3H,6aH,9H,10H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.940   0.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.732  -0.135   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.300   0.433   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.976  -1.798   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.171  -3.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.543  -2.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.291  -1.128   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.802  -1.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.725  -0.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.989  -2.951   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.459  -2.227   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.211  -4.112   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.820  -4.034   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.916  -5.623   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.460  -6.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.298  -5.113   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.842  -5.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.547  -7.125   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.362  -8.498   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.090  -7.625   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.763  -9.194   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.929  -6.614   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.517  -7.297   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.224  -5.103   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.298  -3.872   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.366  -3.994   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.034  -2.577   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.569  -2.450   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.226  -1.058   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.349   0.208   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.814   0.081   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.157  -1.312   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       1.182  -2.611   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.654  -3.062   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.270  -1.394   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.680  -4.602   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   36                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   25   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    5   17   24                                             
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₅NO₅

Average Mass

489.6120 Da

Monoisotopic Mass

489.25152 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C\[C@H]2C(=O)C(C)=C(C)[C@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]23[C@H](OC(C)=O)\C=C\[C@H](C)C1=O

InChI Identifier

InChI=1S/C30H35NO5/c1-17-10-9-13-23-28(34)20(4)19(3)26-24(16-22-11-7-6-8-12-22)31-29(35)30(23,26)25(36-21(5)32)15-14-18(2)27(17)33/h6-9,11-15,17-18,23-26H,10,16H2,1-5H3,(H,31,35)/b13-9+,15-14+/t17-,18-,23-,24-,25+,26-,30+/m0/s1

InChI Key

ZLQPFOHITPCQQO-QCKAJGFESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylaria longipes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Not Available

Direct Parent

Cytochalasans

Alternative Parents

Substituents

Cytochalasan
Carbocyclic cytochalasan skeleton
Isoindolone
Isoindole or derivatives
Isoindole
Isoindoline
Cyclohexenone
Benzenoid
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Pyrrolidine
Cyclic ketone
Secondary carboxylic acid amide
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146683451

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate (NP0244099)

MOL for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D MOL for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D SDF for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D-SDF for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

PDB for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D PDB for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

SMILES for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

INCHI for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

Structure for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D Structure for NP0244099 ((3s,3ar,6ar,10s,12s,15r,15ar)-3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-6,11-dioxo-3h,3ah,6ah,9h,10h,12h,15h-cycloundeca[d]isoindol-15-yl acetate)